2-(2,6-Dichloro­benz­yl)pyrrolidine-1,3-dione

Huang, P.-M.; Wang, X.-C.

doi:10.1107/S1600536809024970

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1762

doi:10.1107/S1600536809024970

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2-(2,6-Dichlorobenzyl)pyrrolidine-1,3-dione

Peng-Mian Huang ^a and Xiao-Chun Wang ^b ^*

^aCollege of Chemistry & Bioengineering, Changsha University of Science & Technology, Changsha 410076, People's Republic of China, and ^bDepartment of Clinical Laboratory, XiangYa Medical College of Central, South University, Changsha 410013, People's Republic of China
^*Correspondence e-mail: huangpengmian@126.com

(Received 25 June 2009; accepted 29 June 2009; online 4 July 2009)

In the title compound, C₁₁H₉Cl₂NO₂, the dihedral anngle between the mean planes of the aromatic ring and the twisted pyrrolidinedione ring is 79.98 (9)°.

Related literature

For the synthesis, see: Duan et al. (2005 ). For the pharmaceutical properties of pyrrolidine-2,5-dione derivatives, see: Obniska et al. (2009 ).

Experimental

Crystal data

C₁₁H₉Cl₂NO₂
M_r = 258.09
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.8057 (5) Å
b = 9.4388 (8) Å
c = 23.936 (2) Å
V = 1085.74 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.58 mm⁻¹
T = 113 K
0.14 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.923, T_max = 0.944
7528 measured reflections
2562 independent reflections
2400 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.073
S = 1.09
2562 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ), 1017 Friedel pairs
Flack parameter: 0.01 (6)

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024970/hb5015sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024970/hb5015Isup2.hkl

checkCIF report

Comment top

The derivatives of pyrrolidine-2,5-dione possess valuable pharmaceutical properties (Obniska et al., 2009). In this paper, synthesis and the crystal structure of the title compound, (I), Fig 1, is reported.

Related literature top

For the synthesis, see: Duan et al. (2005). For the pharmaceutical properties of pyrrolidine-2,5-dione derivatives, see: Obniska et al. (2009).

Experimental top

The title compound was prepared according to the procedure of Duan et al. (2005). The title compound (40 mg) was dissolved in a mixture of chloroform (5 ml) and ethanol (3 ml) and the solution was kept at room temperature for 15 days. Evaporation of the solution gave colourless blocks of (I).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).

Figures top

Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are presented as spheres of arbitrary radius.

2-(2,6-Dichlorobenzyl)pyrrolidine-1,3-dione top

Crystal data top

C₁₁H₉Cl₂NO₂	D_x = 1.579 Mg m⁻³
M_r = 258.09	Melting point = 409–411 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2881 reflections
a = 4.8057 (5) Å	θ = 1.7–27.9°
b = 9.4388 (8) Å	µ = 0.58 mm⁻¹
c = 23.936 (2) Å	T = 113 K
V = 1085.74 (18) Å³	Block, colorless
Z = 4	0.14 × 0.12 × 0.10 mm
F(000) = 528

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2562 independent reflections
Radiation source: rotating anode	2400 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.029
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 1.7°
ω and ϕ scans	h = −4→6
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −12→12
T_min = 0.923, T_max = 0.944	l = −30→31
7528 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.031	w = 1/[σ²(F_o²) + (0.0337P)² + 0.1572P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.073	(Δ/σ)_max < 0.001
S = 1.09	Δρ_max = 0.28 e Å⁻³
2562 reflections	Δρ_min = −0.27 e Å⁻³
146 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.027 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1017 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.01 (6)

Crystal data top

C₁₁H₉Cl₂NO₂	V = 1085.74 (18) Å³
M_r = 258.09	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.8057 (5) Å	µ = 0.58 mm⁻¹
b = 9.4388 (8) Å	T = 113 K
c = 23.936 (2) Å	0.14 × 0.12 × 0.10 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	2562 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2400 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.944	R_int = 0.029
7528 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.073	Δρ_max = 0.28 e Å⁻³
S = 1.09	Δρ_min = −0.27 e Å⁻³
2562 reflections	Absolute structure: Flack (1983), 1017 Friedel pairs
146 parameters	Absolute structure parameter: 0.01 (6)
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.00935 (11)	−0.15827 (4)	0.039298 (15)	0.02779 (12)
Cl2	−0.01306 (10)	0.14810 (5)	0.231345 (15)	0.02661 (12)
O1	−0.4371 (3)	0.35252 (13)	0.15425 (5)	0.0256 (3)
O2	0.2345 (3)	0.17916 (13)	0.03882 (5)	0.0258 (3)
N1	−0.1077 (3)	0.23490 (14)	0.10180 (5)	0.0172 (3)
C1	−0.2311 (4)	0.35434 (18)	0.12493 (6)	0.0201 (3)
C2	−0.0631 (4)	0.48127 (18)	0.10689 (8)	0.0276 (4)
H2A	0.0514	0.5174	0.1382	0.033*
H2B	−0.1863	0.5582	0.0936	0.033*
C3	0.1211 (4)	0.42692 (18)	0.05958 (7)	0.0222 (4)
H3A	0.0520	0.4604	0.0229	0.027*
H3B	0.3156	0.4591	0.0645	0.027*
C4	0.1017 (4)	0.26745 (17)	0.06376 (6)	0.0186 (3)
C5	−0.2043 (4)	0.09082 (17)	0.11224 (6)	0.0177 (3)
H5A	−0.2735	0.0496	0.0768	0.021*
H5B	−0.3619	0.0939	0.1389	0.021*
C6	0.0205 (4)	−0.00365 (15)	0.13563 (6)	0.0160 (3)
C7	0.1336 (4)	−0.11631 (17)	0.10562 (7)	0.0193 (3)
C8	0.3417 (4)	−0.20312 (18)	0.12690 (8)	0.0255 (4)
H8	0.4149	−0.2783	0.1050	0.031*
C9	0.4416 (4)	−0.17880 (19)	0.18054 (8)	0.0283 (4)
H9	0.5851	−0.2370	0.1953	0.034*
C10	0.3327 (4)	−0.0703 (2)	0.21228 (7)	0.0253 (4)
H10	0.3987	−0.0538	0.2491	0.030*
C11	0.1251 (4)	0.01445 (17)	0.18967 (7)	0.0195 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0382 (3)	0.0230 (2)	0.02216 (19)	0.0038 (2)	−0.0022 (2)	−0.00636 (14)
Cl2	0.0287 (2)	0.0340 (2)	0.01716 (18)	0.0004 (2)	−0.00099 (17)	−0.00597 (15)
O1	0.0261 (7)	0.0286 (6)	0.0223 (5)	0.0089 (6)	0.0024 (5)	−0.0028 (5)
O2	0.0255 (7)	0.0264 (7)	0.0254 (6)	0.0043 (5)	0.0073 (5)	0.0028 (5)
N1	0.0175 (7)	0.0171 (6)	0.0171 (6)	0.0008 (6)	0.0003 (6)	−0.0001 (5)
C1	0.0224 (9)	0.0194 (8)	0.0186 (7)	0.0029 (7)	−0.0033 (6)	−0.0012 (6)
C2	0.0315 (11)	0.0185 (7)	0.0329 (9)	−0.0017 (8)	−0.0009 (8)	−0.0001 (7)
C3	0.0218 (9)	0.0207 (8)	0.0242 (8)	−0.0039 (7)	−0.0037 (7)	0.0034 (7)
C4	0.0177 (8)	0.0227 (8)	0.0155 (7)	0.0009 (7)	−0.0020 (6)	0.0018 (6)
C5	0.0188 (8)	0.0153 (7)	0.0189 (7)	−0.0005 (6)	−0.0016 (7)	−0.0002 (6)
C6	0.0141 (8)	0.0167 (7)	0.0174 (6)	−0.0022 (7)	−0.0003 (6)	0.0030 (5)
C7	0.0185 (8)	0.0183 (7)	0.0210 (7)	−0.0012 (7)	−0.0001 (7)	0.0023 (6)
C8	0.0231 (10)	0.0179 (8)	0.0354 (9)	0.0017 (7)	0.0043 (8)	0.0042 (7)
C9	0.0215 (10)	0.0245 (9)	0.0388 (10)	0.0014 (8)	−0.0007 (8)	0.0156 (7)
C10	0.0221 (10)	0.0303 (9)	0.0235 (8)	−0.0061 (8)	−0.0035 (7)	0.0109 (7)
C11	0.0172 (8)	0.0223 (8)	0.0190 (7)	−0.0021 (7)	0.0014 (7)	0.0031 (6)

Geometric parameters (Å, º) top

Cl1—C7	1.7417 (17)	C3—H3B	0.9900
Cl2—C11	1.7400 (17)	C5—C6	1.509 (2)
O1—C1	1.213 (2)	C5—H5A	0.9900
O2—C4	1.208 (2)	C5—H5B	0.9900
N1—C1	1.389 (2)	C6—C7	1.394 (2)
N1—C4	1.391 (2)	C6—C11	1.398 (2)
N1—C5	1.459 (2)	C7—C8	1.390 (2)
C1—C2	1.508 (2)	C8—C9	1.390 (3)
C2—C3	1.526 (3)	C8—H8	0.9500
C2—H2A	0.9900	C9—C10	1.378 (3)
C2—H2B	0.9900	C9—H9	0.9500
C3—C4	1.511 (2)	C10—C11	1.389 (2)
C3—H3A	0.9900	C10—H10	0.9500

C1—N1—C4	112.99 (14)	C6—C5—H5A	109.0
C1—N1—C5	123.52 (14)	N1—C5—H5B	109.0
C4—N1—C5	123.25 (13)	C6—C5—H5B	109.0
O1—C1—N1	124.58 (16)	H5A—C5—H5B	107.8
O1—C1—C2	127.86 (16)	C7—C6—C11	115.46 (15)
N1—C1—C2	107.56 (14)	C7—C6—C5	122.61 (14)
C1—C2—C3	104.84 (14)	C11—C6—C5	121.91 (14)
C1—C2—H2A	110.8	C8—C7—C6	122.79 (16)
C3—C2—H2A	110.8	C8—C7—Cl1	116.53 (14)
C1—C2—H2B	110.8	C6—C7—Cl1	120.64 (13)
C3—C2—H2B	110.8	C7—C8—C9	119.33 (17)
H2A—C2—H2B	108.9	C7—C8—H8	120.3
C4—C3—C2	104.48 (14)	C9—C8—H8	120.3
C4—C3—H3A	110.9	C10—C9—C8	120.04 (16)
C2—C3—H3A	110.9	C10—C9—H9	120.0
C4—C3—H3B	110.9	C8—C9—H9	120.0
C2—C3—H3B	110.9	C9—C10—C11	119.09 (16)
H3A—C3—H3B	108.9	C9—C10—H10	120.5
O2—C4—N1	123.60 (15)	C11—C10—H10	120.5
O2—C4—C3	128.46 (16)	C10—C11—C6	123.25 (16)
N1—C4—C3	107.93 (14)	C10—C11—Cl2	117.94 (13)
N1—C5—C6	112.74 (14)	C6—C11—Cl2	118.80 (13)
N1—C5—H5A	109.0

C4—N1—C1—O1	171.59 (15)	N1—C5—C6—C11	69.50 (19)
C5—N1—C1—O1	−3.0 (2)	C11—C6—C7—C8	−1.7 (2)
C4—N1—C1—C2	−8.48 (18)	C5—C6—C7—C8	179.66 (15)
C5—N1—C1—C2	176.92 (14)	C11—C6—C7—Cl1	176.23 (12)
O1—C1—C2—C3	−165.92 (16)	C5—C6—C7—Cl1	−2.4 (2)
N1—C1—C2—C3	14.14 (18)	C6—C7—C8—C9	0.7 (3)
C1—C2—C3—C4	−14.26 (18)	Cl1—C7—C8—C9	−177.37 (14)
C1—N1—C4—O2	−179.73 (16)	C7—C8—C9—C10	0.6 (3)
C5—N1—C4—O2	−5.1 (3)	C8—C9—C10—C11	−0.7 (3)
C1—N1—C4—C3	−1.03 (18)	C9—C10—C11—C6	−0.5 (3)
C5—N1—C4—C3	173.59 (14)	C9—C10—C11—Cl2	178.68 (13)
C2—C3—C4—O2	−171.54 (18)	C7—C6—C11—C10	1.7 (2)
C2—C3—C4—N1	9.84 (18)	C5—C6—C11—C10	−179.73 (16)
C1—N1—C5—C6	−123.48 (16)	C7—C6—C11—Cl2	−177.52 (13)
C4—N1—C5—C6	62.46 (19)	C5—C6—C11—Cl2	1.1 (2)
N1—C5—C6—C7	−111.97 (17)

Experimental details

Crystal data
Chemical formula	C₁₁H₉Cl₂NO₂
M_r	258.09
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	113
a, b, c (Å)	4.8057 (5), 9.4388 (8), 23.936 (2)
V (Å³)	1085.74 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.14 × 0.12 × 0.10

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.923, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	7528, 2562, 2400
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.073, 1.09
No. of reflections	2562
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.27
Absolute structure	Flack (1983), 1017 Friedel pairs
Absolute structure parameter	0.01 (6)

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

Acknowledgements

This work was supported by the Changsha Science and Technology Bureau (k0803061-11) and the Scientific Research Foundation of Hunan Provience (S2007F123).

References

Duan, X. M., Han, J., Chen, L. G., Xu, Y. J. & Li, Y. (2005). Fine Chem. 22, 39–40, 52. Google Scholar
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Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
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